$300 Tramp For Hire

Stephanie was an old flame who lived in Boston. She was very sexual, and that year she was down on her luck.

On a visit to Boston, I made an indecent proposal to Stephanie. I offered to pay her $300 to help you and I cross a new virginity barrier. She needed the money, but didn't agree at first. I explained the history and what you and I were trying to accomplish. I made it clear that it would be a great service to you (a wonderful, but inexperienced person who deserves sexy treatment, mind blowing orgasms, and a chance to take risks).

Stephanie agreed only because she liked the way I had described you.

I told you to expect a surprise, and when Stephanie and I knocked on your door. . . your mind was racing. A few glasses of wine later, and I was kissing you in front of her. It's still a bit awkward, so I take control. I tell you to remove your pants and panties.

You undressed . . . half in shock and polite on auto-pilot. I sat you back on the couch and started kissing you again. I looked back at Stephanie, and motioned to her to start licking your pussy.

I kissed you intensely to keep you distracted. There was a pause, and I heard the rustling of Stephanie removing her clothes behind me. While kissing your suddenly trembling lips -- I could tell when she made contact and started pleasuring you.

I sucked on your neck, bit your shoulder next to your bra strap, and then moved away. Your eyes were closed. From your expression, I can't gauge discomfort versus pleasure. She was paying you a lot of attention. I looked down. I saw her fingering you lightly, and your love was very swollen pink under her flicking tongue.

She kept looking up at me, but her mouth never left your clit. Such a slut. The $300 was just her excuse to do this. She was really getting off on crossing into your new sexual territory. She was wearing eye makeup, and she looked very natural eating out a girl. Intently looking up with a lusty expression, she was on her knees. She was naked except for panties.

I heard you moan, and I stood on the couch. Quick unzip before I brushed my cock on your cheek. I wanted to get your attention, so I patted it softly on your lips. I knew you not that experienced at sucking dick, and that's why I told you to stick out your tongue. I rubbed on cock on your open mouth, but I resisted the urge to shove it in.

I was rock hard, and my balls were starting to get sore from the vivid sex show in your living room.

I wanted you naked, so I unfastened your bra and pulled up your shirt. Your eyes opened for the first time since this started, as you helped me undress you. You were staring at Stephanie, and she was working it. She started fingering you faster to let you know she was in control of the coming ecstasy. Your head rolled back, but I grabbed the back of your head and without a word communicate that I wanted you to watch Stephanie lick your very excited pussy.

My balls were so sore. I want to cum too.

While seated next to you, I started stroking my cock and leaning in to suck on your breasts. I popped your nipples in and out of my mouth and grazed them with my teeth. After 30 seconds, you shuddered in a violent thrust and involuntarily pulled Stephanie's head into your mound. So assertive when you cum.

You were out of breath and flushed. I pushed Stephanie out of the way, so I can relieve myself inside you. I fucked you hard and deep. I told Stephanie to work on your breasts. "Let's make her cum again" I directed.

Your eyes were closed again. So much stimulus that you could barely take it. I was pumping your inexperienced pussy without mercy, but you were so wet that it doesn't matter. It was too good. The tightness of your pussy. The sight of the two of you. I pulled out and shoot my load across Stephanie's cheek. You laid there. . . out of breath.

After a nap, I awoke to the sounds of Stephanie working on you again. Her brown hair was falling over her face as she fingered and lapped. I positioned myself behind her, and worked my cock inside with slow, deliberate strokes. Her cunt was noticeable looser than yours, and that made me think of how experienced she was. I had made the right decision in hiring her.